Middlesbrough boss Gareth Southgate insists Stewart Downing is better than Tottenham and should be aiming higher, after the club rejected bids from Spurs for the England star this week.
The North London club have a long-standing interest in Downing, dating back to 2005, but they have never been able to prise the 24-year-old away from the Riverside.
"I don't think it [a move to Spurs] is in the interests of our club or in the interests of Stewart," said Southgate. "There's a certain level that, if Stewart's going to leave this club, he should be going to.
"I'm not knocking Tottenham but I've had plenty of conversations with Stewart about his future, the majority of which I'd prefer to keep private. He totally understands I want the best for him."
Southgate admits that if Boro had been more secure in the league, rather than fourth from bottom, they may have been more inclined to let Downing leave.
"If we'd had seven more points now it could quite possibly have been a different situation," he said. "I've had several talks with Stewart this week and he knows I can't put him first at the moment.
"Timing is the key issue. Stewart is such a talent, such an important player to us that, at this time of year, there's no way of replacing him. We'll be a lot more sympathetic to players at the end of the season when we have time to adjust plans but it's very difficult to bring replacements in during January."
Southgate also stressed it is not easy adding to his squad, as he appears to be trying to lure both Ben Watson from Crystal Palace and Newcastle's Alan Smith - in a possible swap deal with Mido - to the club.
"It's difficult to get players to come to a club such as ours and particularly when we're in our current league position," he said. "There was a time when we paid the sort of wages very few other clubs were paying but that's not the case anymore."